The One Thing You Need to Succeed

The One Thing You Need to Succeed

I used to hate the ‘F’ word. I cringed each time I thought of it and felt an overwhelming sense of unease every time I felt as though it might be creeping into my life.

I have since learned how essential that one tiny ‘F’ word is to my personal development; because without failure I wouldn’t be where I am right this very minute.

Oh. Wait. Did you…? You didn’t think I meant I hated THE ‘F’ word did you? Fuck no! I love that word! But today I’m talking about my other favourite ‘F’ word – failure – and why it is utterly crucial to embrace it in order to become who you truly wish to become.

Get ready for a story because I have a lot to say…

My Road to Failure

Deep down inside I have always had the entrepreneurial itch. I always craved the freedom and I have always, I repeat, ALWAYS hated being told what to do.

So it was only a matter of time before I tuned into that deafening whisper within me and started baby-stepping Β my way towards a lifestyle where I was in charge of calling the shots.

But it wasn’t easy. In fact, my path has been fraught with trials and triumphs, cringe-worthy moments and happy tears, nerve-shattering anxiety and relief.

About 7 years ago I had an idea for a TV show I desperately wanted to pitch. It wasn’t anything new but there also wasn’t anything like it on TV – it was called TwentySomething TV and it was essentially a mix between The View and Sex and the City.

One fateful day I met a producer at a commercial audition I was up for where he asked me to tell him one exciting thing I had going on in my life at that moment. Never having been asked this before I immediately answered “I’m writing a TV show!”. He was intrigued, we swapped numbers and met the following week where I pitched him my idea – hands shaking and sweat drenching my super-cute dress.

I remember it like it was yesterday. This was the first time I had actually taken the first step to doing something I loved, something I believed in and I had all the confidence in the world that this show would be an easy sell.


To clarify, the producer agreed to partner with me and we decided to test the show out online before approaching a TV network. Well, that was in 2006, aka the days of MySpace and wellll before online video was a viable way of getting noticed.

Throughout the years that show was online we amassed close to million views and had some key potential sponsors come and go (AOL, Johnson & Johnson and Durex to name a few) but after 24 months and nearly 10k lost on my part (and my producer’s) we decided to stop production and part ways.

I felt an overwhelming sense of failure and disappointment for letting our team down. But I shook it off.

Next up was another web show I created with a girlfriend of mine (and co-host on TSTV) featuring our travels through Australia. Again, we dedicated time and money to a dream we believed in. We partnered up with the Gold Coast tourism board and had an absolute blast, but there was no money there.

And for the second time in 2 years I found myself struggling to figure out what to do with my life. I was 28 at this point and freaking the fuck out that I had no direction, no money and some pretty hefty debt.

I fell back on a job bartending – something I had done for 8 years on the side and absolutely loathed – slinging drinks for a few measely dollars and a whole lotta headaches.

Fortunately, my boss was interested in video marketing and sought me out to meet with him and his wife and discuss how they could utilize online videos for their 3 restaurants.

Finally I saw an opportunity: These two had 3 successful venues, an open mind and money to spend.

I pitched them a monthly package that included social media management, weekly videos, blog posts and a new site to feature it all on.

To my relief they accepted my pitch and just like that I catapulted myself out of bartending once and for all and signed my first client.

Not even five months later my finicky client turned on me, cut my fee in half while keeping my partner at her full rate. It was a devastating blow to my confidence, not to mention my bank account, and those familiar feelings of failure started creeping back in.

For the next 6 months I struggled…a lot.Β I had even less money than before, was brimming with resentment and felt flat out defeated.

So I started hustling: I spent all day learning, writing and building a name for myself as the go-to gal in hospitality social media marketing.

When I finally moved back to Toronto I was ready to hit the ground running. I took everything I had learned, contacted venues I thought I could help, set up meetings and signed my first 3 in one day.

I was thrilled!

7 months later I was burnt out and looking for a way out.

I was furious with myself.

After all, this is what I had been hoping to achieve all along: A thriving business with great (albeit a tad overwhelming) clients and enough income to hire someone to help me manage the workload and allow me to only work mornings.

So what the hell was wrong with me?

I realized I was craving freedom – freedom from client requests and contracts; freedom to go wherever I wanted, without having to clear it with my clients prior to stepping on a plane; freedom to scale my efforts past a few thousand a month and make as much as I wanted to make, without having to burn the candle at both ends.

Fortunately, Josh was already living that lifestyle.

We decided to team up and start anew.

We started at square one with a brand new site, no readers, no rankings and no sales. We decided we would stick with what Josh new best at that point and started creating thin affiliate sites – sites with maybe 3-5 posts on them, shitty backlinks and no thought or care put into them.

Within 2 months we made our first sale of $20 and figured the money would quickly start rolling in.

Not so much.

Our sites got slapped by Google, we were banished to the barren depths of page 5 and our we were burning through our savings, fast.

We stressed, we fought, we paced, we drank and we wondered if we should entertain the idea of getting jobs – an unthinkable compromise and one we resented even having to consider.

We felt depressed and lost and knew something had to change.

The Stepping Stones of Failure

Thankfully, one sunny morning we decided to get out of our apartment, go for a walk and figure shit out.

We started by recounting all the steps we had taken that hadn’t worked up to this point and decided to do something drastic – we pivoted.

From that moment on we switched our focus to a new and unfamiliar path – one where “good enough” was no longer good enough. We realized that we had to stop trying to avoid failure and instead accept that it would come – as it always does when you want to transition from good to great.

We embraced our failures, forgave ourselves for our mistakes and chose to learn from them. We focused on creating a voice, a brand and a community and built a website that readers wanted to come to.

Was it easy from there on out? Hell no! It still isn’t.

In fact, we fail all the time – from new niches we try to enter that fail to linking practices that have a negative effect on our rankings to hiring the wrong people for the wrong jobs.

We fail a lot. But what’s crazy is we WANT to fail!

We revel in the opportunity to fail.

And we bear-hug it and appreciate it for what it is – the source of our most formative lessons, the key to becoming more confident in our business and the sign that we are on the right path.

I mean, think of it this way: if you are failing, you are following in some pretty rad footsteps…

Famous Failures

Maybe it’s just me but if there is one thing I relish in with my professional growth, it’s seeing where others have come from.

For example, did you know:

  • The Beatles were initially told “we don’t like your sound, and guitar music is on the way out.”
  • Steven Spielberg dropped out of junior high school, went back and was placed in a class for those with learning disabilities only to drop out for good a month later.
  • Michael Jordan was cut from his high school basketball team because of “a lack of skill”.
  • Bill Gates was a Harvard University dropout and his first business “Traf-O-Data” tanked.
  • Henry Ford’s first 3 businesses failed before hitting the jackpot with Ford in his 50’s.
  • Walt Disney was told he “lacked imagination and skill” and actually went bankrupt 4 times before succeeding
  • Marilyn Monroe was fired by 20th Century Fox a year into her contract after her producer told her she was unattractive and couldn’t act.
  • Abraham Lincoln failed campaigning 7 times before finally becoming the US President.
  • Elvis Presley was told by the Grand Ole Opry manager “You ain’t goin’ nowhere, son. You ought to go back to drivin’ a truck.”
  • Oprah Winfrey was fired from her job as a reporter after she was told she was “unfit for TV”.
  • Thomas Edison (who has 1,093 US patents under his name) was initially told he was too stupid to learn anything and it took him nearly 9,000 attempts before he finally created a working lightbulb

And those are just 11 off the top of my head!

You see, everyone who has greatness within them and wants to live a life they love is bound to fail, to have to start over and check their ego at the door if they truly want success.

They have to be willing to wade through the exhilaration and anxiety, celebrate the joyous triumphs and brush off spirit-crushing defeats, experience the elation and frustration and foster unwavering strength and vibrant resilience.

It is part of the perfectly imperfect journey.

And it is not for the faint of heart.

So, fail. Fail often. And fail fast. It is the only way you can emerge into the person you are truly meant to be, no, the person you deserve to be.

Thanks for reading.

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21 thoughts on “The One Thing You Need to Succeed”

  1. I couldn’t agree more Jill, great post. I really appreciate you sharing your journey because I think many people make the mistake of thinking you can go from zero to hero with no hiccups.

    I know from my personal experience that I’ve failed countless times, and I’m sure I’ll fail again and again, but that doesn’t mean you have to stop trying πŸ™‚ I read that the famous baseball star Babe Ruth had the highest number of home runs in 1923. In the same year though he also had the highest number of strikeouts. If you try more, you’re gonna fail more, but your probably also gonna succeed more too πŸ™‚

    P.S. I’m coming to Chiang Mai next month BOOM πŸ™‚

    • A-freakin’-men Eddie! Love the “if you try more, you’re gonna fail more, but you’re probably also gonna succeed more too”! So bang on, and I totally agree.

      Do I think I’m done failing? Hell no! I’ll probably fail at least a couple more times this year alone, and that’s okay because those failures will just get me one step closer to my end goals πŸ™‚

      Thanks for the comment.

      And hit a girl up when you get to CM! We’ll be in Malaysia until Sept. 16th but back in action after that! Holla!

  2. Hey Jill!

    I seriously considered if you meant f.u.c.k for 3 secs but I knew it can’t be, so I had to click through and find out what is the f word that you used to hate πŸ™‚

    Thank you for sharing your journey with us and I am happy to hear that I am not alone in terms of the cycle of creating, failing and learning. Its not what I aim for but I accept that its part of the journey of creating the life that’s worth living.

    By the way, I created a little game with my wife, we are launching the app in Sept, and if we are able to make 1000 euro by the end of 6 months, she would quit her job, build the business and travel around Europe in a car with me πŸ™‚ πŸ™‚

    Keep writing these awesome posts, i am lookin forward to reading them!


    • Nice! I love that game…way to finagle your ideal end result there πŸ˜‰

      And thank you Brian, I really appreciate that…and no, you are DEFINITELY not alone. In fact, each successful person I have met so far has had a looong road to get to where they are. It’s never an overnight journey and it’s usually not even the initial business they start out with that makes them successful.

      That’s why I love hearing other peoples stories (and sharing my own) because it can lend such useful perspective and make you realize it’s not just you who has had to battle for your dreams πŸ™‚

  3. Hey Jill!

    Great post. So many people hit that first F and quit right then and there. They never know what could have been.

    I believe we are who we are today because of the yesterdays, good-bad-indifferent. Without them we don’t learn, yearn or strive for better. So all those things we go through, all those losses of money, time, energy and thought are all the building blocks of what we have now. And wouldn’t we be pretty boring without all of those stories to tell?!

    • I love that Fawne! Yes, we would be frighteningly boring…after all, all those stumbles equip us with amazing stories to tell down the line. Or at the very least give us some wicked perspective πŸ™‚

  4. Great post! I’m in the midst of closing down my first business now and needed this. The best inspiration is that Colonel Sanders started KFC with he was friggin’ 65, that stubborn old coot.

    Fall seven times, get up 8 — and you win!

  5. Inspired post! Never thought that so many successful people failed so many times before hitting the jackpot!

    It’s really a nice F to start your journey with and hopefully can end with an S (success). Long way to go!

    • I know, right? I felt the same way and found their failures incredibly encouraging so I had to include them πŸ™‚

      I just think it’s crucial for us crazy entrepreneurs to know what other successful people have been through (and still have to go through!) and that we’re not alone in our struggles to make it.

  6. It’s so cliche, but it really does take an epic fail or two (and plenty of little ones) to appreciate the value in them.

    There’s a fine line between success and failure. I was seriously at the lowest low the week before my highest high.

    The hardest part is knowing when to write those F Bombs off and move on.

    • Greg, love that! And while I don’t know your story in-depth, what you and the wife did share was incredibly inspiring. You just never know when things are going to take a turn for the awesome πŸ˜‰

      Thanks for the comment!

      p.s. Josh and I are SERIOUSLY hooked on Focus at Will lol!

      • And can’t help but jusssst stumble on this:

        Jon Oringer, 39, founded 10 companies before he hit on the idea for Shutterstock, the successful stock-photo website that has made him Silicon Alley’s first billionaire.

        “I’d failed a whole bunch of times before that and I was willing to fail again,” says Mr Oringer of his decision to go into the photography business, something he knew nothing about.

        • Oh I love that! Thanks for the link Greg, reading now πŸ™‚

          Have I mentioned how much I love hearing other entrepreneurs stories? Cuz I do!

  7. Its been quite the journey hasnt it Jilly! Its been an exciting ride and I have made countless friends sit with me while I make them watch TSTV ( this frightened my 18 year old engineering friends) , Do the Roo , Social Media NZ etc etc. We are so proud of what you have accomplished and are excited to see whats next!


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